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Journal Article
Research Support, Non-U.S. Gov't
Asymmetric Catalytic [4 + 2] Cycloaddition via Cu-Allenylidene Intermediate: Stereoselective Synthesis of Tetrahydroquinolines Fused with a γ-Lactone Moiety.
Organic Letters 2018 April 7
A decarboxylative formal [4 + 2] cycloaddition reaction between ethynyl benzoxazinanones and 5-substituted 2-silyloxyfurans catalyzed by chiral Cu-Pybox complex is described. This method allows the formation of intriguing tetrahydroquinolines fused with a butyrolactone moiety featuring three contiguous chiral centers in high yields with excellent diastereo- and enantioselectivities in most cases. The utility of this method was exemplified by the removal of the N-protecting groups and derivatization on the terminal alkyne functionality of the cyclization products.
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